13 Unlucky Lessons

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Introduction
Retailers are presented with ever increasing competitive and
economic pressures to do more with less. Now, with
pervasive trends such as consumer tablets and smartphone
devices, retailers are looking at how to use this technology to
enhance revenue. In fact, recent research suggests that up to
99% of retailers are using or are planning on using mobile
technology to enhance their profitability. This whitepaper
highlights lessons technology veteran David Sipp and other
retailers have learned from their Mobile Point of Sale
deployments. In addition to stating the challenges of iOS and
other consumer devices in enterprise retail environments,
the whitepaper also outlines several things to consider before
searching for a Mobile POS solution.
Workflows Drive the Technology
Implementation vs. the Implementation
Driving the Workflows
Mobility is a tool in service of an improved customer
experience. Attention should be focused on avoiding
implementing mobility in places where it is not needed or
doesn’t fit. Consider specific workflows that will enhance
sales and customer loyalty, then architect solutions to fit
these.
Don’t buy software or services that force you into a pre-
defined workflow. Every retailer has unique needs and a
custom implementation. Continue to develop specific
solutions for your needs.
For example, removing cash-wraps because they take up
space is not really a new workflow. And it may force you into
a Mobile POS system with a more cumbersome process if
merchandise needs security tags removed or counter space is
required for bagging merchandise. If countertop systems are
used often, then consider mobile devices as a supplement
and not a replacement.
Introduce Change at a Pace that
Matches Your Workforce
One of the most common tenants of organizational behavior
is that people resist change. When considering a Mobile POS
solution, gauge the willingness of store managers and
associates to embrace new practices. A staff that feels that
too much is changing, especially if the benefits of the
alteration to the staff or customers isn’t obvious, will be
resistant to the change.
To assess your staff’s willingness to accept change, consider
two different aspects. First, what are the demographics of
your store personnel? Are they tech savvy people working in
like-minded chains, like electronics or young fashions? Or,
are they established, tenured salespeople? Are they
generally comfortable with mobile computing? Will they
accept carrying a tablet or other mobile device? Historically
resistant retailers include auto-parts, hardware, furniture and
interior design, as well as long-established clothing brands
and department stores with established sales people. If the
front line employees are unionized, the union may take a role
in determining how the changed workflow affects their
members.
The second consideration is how much variation will you
introduce? If you are switching from an incumbent
application with counter-based cash wrap to an all-mobile
based system with new software and processes, associates
who have exhibited eagerness for change are most likely to
be successful. Otherwise, the magnitude of these changes
will disorient most people and make them uncomfortable.
Smaller, incremental changes are more likely to succeed, for
example: instead of replacing all countertop systems, instead
add mobile devices that run the same operating system and
thus the same software as the countertop systems. This
allows associates to use the mobile devices when they feel
they add value, rather than feeling that the devices are
forced upon them.
iPads/iPhones are Intuitive as Consumer
Devices, but for Enterprise Use...
Deploying any device in a retail environment requires a deep
understanding of how the systems work, how they interface
into corporate databases, and how the software works.
Don’t underestimate the effort to deploy ANY new device or
capability. Underestimating iOS devices comes from the fact

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that while iPads and iPhones are intuitive as consumer
devices, this does not translate into easy-to-deploy or easy-
to-use in a retail setting.
Why? Mainly because in retail, they are not used as
entertainment devices. Instead, they are running
sophisticated retail software applications designed to drive
all the steps of a transaction. Cardholder data has to be
protected and the PCI guidelines need to be followed.
Network connectivity is critical – a network dropout while
consuming entertainment is mildly annoying, a network
dropout during a transaction breaks the session and may
result in immediate lost sales.
If you were to switch from Windows to Linux, you’d hire
Linux experts and train existing staff. Likewise, if switching
from Windows to iOS, you need to obtain and develop the
expertise for this platform. Don’t assume that the
familiarity of some technical staff with iPads translates into
expertise using them in a commercial environment.
Technical staff needs skill with: OSX, Apple Configurator,
iPhone Configuration Utility and Xcode. Also, some MDM
(Mobile Device Management), MAM (Mobile Application
Management) and MCM (Mobile Content Management)
support will have to be installed.
Additionally, iPads and iPhones are designed to be single-
user devices. Introducing them into a multi-user
environment brings additional challenges in managing
profiles for these devices. This lack of multi-user support
becomes a big issue with Shift and Seasonal workers during
holidays, and during times of heavy turnover.
In-Store IT Support
Another consideration is how to provide 1st level support
for stores. Most retailers have established software and
processes refined over a decade or more. Trained 1st-level
staff are available to assist with enterprise software and
POS. In many cases a new sales associate will ask a veteran
associate about how to use the systems and they’ll get
good advice. However with a change to iOS devices, the
protocol changes and new ways to interact emerge.
Inevitably, there will be differences, like how to accept a
return if the product is now on sale. Since there is new
software, it is new to everyone in the store, so organic
support of experienced users is not available. Worse,
associates with misplaced confidence – people who are
very comfortable with Apple devices for home use may
think they can easily manage these same devices in a
commercial setting. For example, you may have set-up a
controlled Wi-Fi subnet for these devices and a store
associate may connect instead to the Guest network. Or
maybe they’ll try to download an unauthorized app, or
change other settings. These same people would never
think of going into the settings of an IBM or Fujitsu cash
wrap, but an iPad is seen as an easily manipulated
consumer device.
MDM (Mobile Device Management) allows items like
cameras to be removed from iOS along with other items
like iTunes, Safari, etc. Those who have no experience with
MDM have assumed that the device is corrupt or otherwise
malfunctioning. This has led to in-store personnel
performing full factory resets, or have taken devices home
to be plugged into personal PCs for troubleshooting.
And since iOS devices don’t have effective lock-down
modes, users can intrude in areas that you don’t want them
to. With iOS devices, whoever has physical possession of
the device controls the device.
Lastly, there are device management costs. For example, if
your iPad becomes corrupt, you’ll need to connect it to
something like an Apple Mac Mini to run the Apple
Configurator tool to reimage the device. This can be a
$1000 cost per store, plus you need to train someone to
run the configurator. You’ll be training your staff to be
technical, and not on selling.
The Case for Cases
Consumer devices are not designed for the rigors of a retail
workplace, so many retailers have tried to enclose the
devices in protective cases.
One reason for these cases is to try to prevent
unauthorized people from accessing the buttons to control
the consumer device. Look for cases that fully enclose the
device. Some cases have small gaps or pinhole openings.
Retailers have seen instances of people inserting paperclips
or the edge of a credit card to get access to the controls.
So look for a mobile device where the buttons can be
software disabled, or look for a case that fully encloses the
tablet or other mobile device. Note the downside here is if
the device needs to be accessed by the sales associate, a

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key must be found (“Where is the manager?”) to open the
case.
Another obstacle is that carrying cases are mated to the
exact dimensions of the consumer device. These device
manufacturers are primarily focused on consumers, not
business, so in their quest to quickly update to the latest
technology, they will often change the dimensions of the
mobile device. Tablets get smaller or bigger screens, new
generations are often thinner, and connector formats can
change. So either choose a mobile device from a
manufacturer with a commitment to not change the form
factor for a number of years, or expect to stock different
cases for different versions of your devices.
Consumer Devices – Prone to Theft
Most computers in retail stores are not attractive to
thieves. Even though stationary POS systems are often
a PC at the core, they are specialized products. The
gray market for commercial devices is very limited
because most reputable businesses would never buy
commercial-grade equipment from a questionable
source.
That is not the case with consumer devices. These
devices have a trio of characteristics to make them
desirable to thieves: They are instantly recognizable as
consumer devices, they have limited theft-prevention
capabilities, and there is a large gray market for stolen
devices.
These devices are also relatively small and are
commonly laid down when performing another task. A
quick distraction and the device is left for the taking.
This is especially true for iPads which are too big to be
placed in a pocket by the associate.
Retailers should expect attempts to hack the device
used as kiosks. Retailers have experienced mischievous
shoppers or others attempting to show off there iOS
skills to friends or worse, attempt to remove the devices
from the protective cases leading to many iPads being
damaged.
Anticipate Customer Response
Another constituency that has to accept mobile devices
is your customers. Think about how mobility will
enhance the customer’s experience. Many customers
expect to find a cash wrap station. It is a home base, a
place where they know that they can find help.
Sometimes customers are wary about using a mobile
device to swipe their credit card, especially if the sales
associate only approaches them to check them out. In
contrast, a workflow that helps the customer, perhaps
by showing alternative or complementary products, or
scheduling delivery, for example, is value-add for
consumers, and they immediately see the benefit of the
service. If the end of this process is the payment, it will
then be natural for the customer to hand over their
credit card.
In contrast, a mistake some stores have made is to have
a casually dressed associate approach a customer “cold”
and offer to take payment for the items. Many
consumers are immediately concerned that this is a
scam.
You Still Need a Cash Wrap Station
Mobility in retail can add many useful workflows. Some
of these are Assisted Selling, Line Busting, and mobile
POS for additional lanes or pop-up stores. But in many
cases, a retailer will still need to retain some of their
traditional counter-based cash wraps.
Plan to retain many of your existing countertop cash
wraps. You’ll need a place to remove tags, bag
merchandize, print receipts, etc. Yes, consumers can
choose email or texted receipts – but be aware that
many won’t want to do this, many consumers still want
the paper receipts. Also, you already have the receipt
printers, cash drawers, etc. Plan to use them, even as
you deploy mobile devices.
Often more important, consumer’s see the cash wrap as
a Home Base, especially in larger square-foot stores.
They expect to see them in stores, it is where
consumers go to talk with sales help or make returns.
Some retailers have removed the cash wraps or hidden
them, and there has been a noticeable lack of comfort
with some shoppers. Even Apple has cash drawers in
their stores.

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Additional Investment in Wireless
Network
Consumer devices are great content consumption
devices. In a retail setting the enterprise software
usually requires significant local storage and working
space for databases of items and the queuing of
transactions. Since consumer devices generally have
limited internal capacity for these large working sets,
the typical installation uses the network for cloud
access. This works fine when the network is available.
One pitfall to avoid is an incomplete or inadequate
wireless infrastructure. With always-connected wireless
devices, you need to avoid any dead spots in your
network in each store. This isn’t just an inconvenience.
With some retail software, a session will be broken with
a network drop, resulting in the loss of the current
activity or the need for the associate to re-authenticate.
Getting a robust network with complete coverage
requires professional network services. Some retailers
have reported that the cost of a sufficient network
upgrade and implementation was the single largest cost
of going to mobile POS.
You also need to consider the radio-capability of your
mobile devices. For example, one retailer found that
their existing network needed significant upgrades.
They found that their WAP (Wireless Access Points)
could transmit further than their iPads could transmit
back. The iOS radios were further attenuated by the
sleds that were attached. Since iOS radio systems
cannot be tuned, all work has to be done on the
Wireless network side. Access point power levels will
have to be tuned to provide proper power level across
the store without the access point interfering with each
other.
Another issue is with roaming: when a mobile device
moves from one access point to another. It has to be
seamless! One strategy has been to use OPK
(Opportunistic Key Caching), but be aware that iOS does
not support this, so the device will have to re-
authenticate each time it switches WAPs, causing a lag
in app performance and may cause session drops.
In order to avoid this limitation you must run your
software on devices that have the capacity to operate
even with the network down. Alternatively, do a
detailed audit of the current wireless infrastructure in
your stores, and plan for a network upgrade or
replacement, and many months for tuning the system.
Some retailers have had to install 2 networks, one for all
their guests, and another for store functions since the
store’s iOS devices could not tolerate drops in
bandwidth. The second Guest network can then also
serve as a backup if the MPLS (Multiprotocol Label
Switching) link went down.
Many prudent retailers have implemented sophisticated
schemes to keep stores operating even if network
access fails. These systems often can run
independently, scan all items in the retailer’s database,
and even queue up transactions for a batch-load when
the network returns. But mobile POS systems that rely
on constant network access will fail during a network
failure. Some of these network failures can be
significant events. Consider Hurricane Sandy in October
of 2012: in Northern NJ and southern parts of
Manhattan and Long Island, networks were down for
days or weeks. Some retailers were still able to operate
in these cases because their software ran in its entirety
on the systems in the physical stores. A store that had
to have network connectivity was out of business for
those days.
Integration with Enterprise
Information Systems
This can be a significant issue to overcome: applications
that are information islands, or not connected to
corporate databases fully can compromise the integrity
of your data. Most retailers have sophisticated systems
that have been established over many years to allow
headquarters to see real-time activity, manage
inventory, plan inventory replenishment, and do many
of the “Big Data” functions. Your incumbent software
provider may not be an iOS developer. Bringing in a
separate retail package can force a choice between a
wholesale switch to the new provider, or developing
new methods to connect the 2 systems.
Save Money—Leverage Existing
Accessory Investment
Receipt Printers, Cash Drawers, Scanners and Payment
Terminals are needed in most mobile workflows.
Obviously, you need devices that work with your mobile
device. Bluetooth and Wi-Fi are reliable connection
methods. But you also need to consider the interface
software. Do you want to use OPOS (OLE for Retail POS)
drivers to access your accessories?
Retailers already have an extensive amount of
accessories throughout their stores. These devices are
almost all based on Microsoft Windows drivers. (OPOS
is built on Windows.) If you move to a consumer device,
you will need to replace many or all of your accessories
to get ones that are supported by Android or iOS. Most

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suppliers of these peripherals have added devices that
connect to consumer devices, however there are
generally only one or two to choose from.
If you use a Windows-OS mobile device, you can often
still use most of these devices. Whether connecting
physically when docked, or wirelessly, the same
Windows drivers can access these devices. Also, many
wired peripherals can be converted for wireless access.
For example, some printer manufacturers offer
upgrade modules to convert them to Wi-Fi. In other
cases, Ethernet devices can simply be attached to
wireless router and become available to mobile
devices.
Another thing to consider is that using iOS as a
platform may drive you to peripheral suppliers
different than those you currently work with. Where
you have established satisfactory delivery, service and
payment term contracts with your current suppliers,
you may have to start working with new suppliers and
new distributors.
PCI Compliance – Make sure your
OS+App Combo is Certified
Accepting payments on mobile devices often requires a
new PCI (Payment Card Industry) assessment of all the
systems in use. And since, per PCI Council rule
payment applications on consumer devices cannot be
PA-DSS (Payment Application – Data Security
Standards) certified, a new system to lessen the risk of
cardholder data breeches needs to be developed and
PCI risks assessed.
One way to avoid this pitfall is to use a commercial
grade device that runs the same OS as was certified
with the PA-DSS application. This can greatly lessen
incremental PCI work and assessments.
Note that as of August 2013, there are 2570 PCI
certified PA-DSS applications, across 28 different
operating systems, there are none (0) for iOS or
Android. A move to iOS requires a new PCI compliance
plan without the benefits of PA-DSS technology.
Payment Processing – Prepare your
Organization
Another pitfall is a mobile device that forces you into a
new payment processor or credit card system. This is
often necessary since a move to P2PE (Point to Point
Encryption) is required since traditional methods to
protect cardholder data aren’t possible, such as the
use of PA-DSS applications. There are often many
reasons why you may want to change processors, but
switching because of a move to mobile POS is not
enough of a reason. If you like your current
arrangement for processing credit and debit cards, you
can probably continue to use it.
Sleds (large, attachable plastic pieces with mechanical
connection features) can be used to connect credit
card readers to mobile devices. Often the attached
device talks to the tablet via Bluetooth (BT), 30-Pin
connector or via the audio jack. Since the data
transmission can be compromised, the card reader
usually encrypts the data. This P2PE (Point to Point
Encryption) method usually represents a change to a
retailer’s current payment processes, and may require
a new payment gateway or a new charge per
transaction for encryption services.
Reduce Risk by Reducing Number
of Variables
Most of the pitfalls discussed in this whitepaper will
need to be addressed if you are adding iOS-based
mobile POS to an established retail environment.
There is a lot to consider and a lot to plan.
There is also the issue of timing. The timing of all of
these actions converges on the day of the rollout in a
store. And as each slice of each category gets closer to
the center (deployment), the available man-hours
decreases and the inter-functional communication
ramps up as critical issues crop up.

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Conclusion
There are many advantages to mobile technology in a
retail setting. Start by focusing on workflows with clear
benefits to operations or to your customers’ needs.
Once they are set, consider how to minimize the
disruptions that happen with the introduction of these
mobile workflows. Be wary of providers who offer a
stand-alone solution to address some of these
workflows, they often force retailers into entirely new
processes, and purchases of new accessory devices.
Most retailers have already invested in significant IT
capabilities, including database connections for real-
time business analysis. The in-store POS systems are
proven reliable and are specific to your retail needs.
Retailers have standardized on specific receipt printers,
payment terminals, scanners, etc. IT has developed a
wealth of skills managing the entire infrastructure. All
of this represents a huge investment. This investment
has paid off in terms of a reliable, scalable, secure, and
integrated environment. Retailers would be best
served if they choose mobile technology that protects
most of this investment, or even builds on this
investment.
By choosing technology that works within the current
environment, retailers will see other benefits. Change
can be managed and new features can be added
incrementally. With these incremental changes, there
will be less disruption to the core business. Sales
associates and customers alike will experience change
at a more comfortable pace and will be more likely to
embrace it.
Retailers each have a unique architecture, developed
specifically for their business needs. Adding mobile
POS should not force most of the existing methods to
change. Demand solutions that fit your needs and you
will realize the full benefits of a mobile retail
environment.
About the Authors
David Sipp is a 20 year veteran in IT. Having worked in various industries he brings a broad set of expe-
riences to the table. He has spent the last three years focused on Enterprise Mobility and the many
issues companies face as they try to leverage this opportunity. He holds many industry certifications
including MCT and CISSP.
Bob Ashenbrenner has more than 25 years of computer engineering and engineering management
experience, with 15 of those specific to mobility and 3 of those specific to retail. Since 2003, Bob has
been with Motion Computing, a global mobility solutions company based in Austin Texas. Most re-
cently, Bob has become Motion’s expert in Point of Sale and payment terminal technologies. In this
role, Bob has led the development of a suite of products, services and software that support retail,
with an emphasis on fitting within a retailer’s chosen environment.